Ethanol → HCID 71203612, compound

HRID 1844558Notes

Reaction equation

HRID 1844558 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].Br[C:21]1[CH:22]=[C:23]([C:29]2[N:33]([CH3:34])[C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:30]=2[CH3:39])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28].C(O)C>C1(C)C=CC=CC=1>[CH3:28][O:27][C:26]1[C:25]([C:8]2[CH:9]=[CH:10][C:5]([S:2](=[O:4])(=[O:3])[NH2:1])=[CH:6][CH:7]=2)=[CH:24][C:23]([C:29]2[N:33]([CH3:34])[C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][C:30]=2[CH3:39])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 71203617HCID 71203617, compound

Product 1

HCID 71203612HCID 71203612, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
97.5 °C

Procedure

4-aminosulfonylbenzene boronic acid (0.72 g, 3.57 mmol) and potassium carbonate (0.89 g, 6.50 mmol) were added to a solution of methyl 5-(3-bromo-4-methoxyphenyl)-1,4-dimethyl-1H-pyrrole-2-carboxylate (10a, 1.1 g, 3.25 mmol) in a mixture of toluene:ethanol (5:15 ml) in a tube at 25° C. Nitrogen gas was bubbled through the reaction mixture for 15 minutes. Tetrakis(triphenylphosphine)(0) palladium (0.18 g, 0.16 mmol) was then added to the reaction mixture under nitrogen atmosphere and the tube was sealed. The reaction mixture was heated at 95-100° C. for 1 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite. The celite cake was washed with 10% methanol in DCM (30 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography using 40% ethyl acetate in hexanes as an eluent to obtain the title compound 10b (0.84 g, 62.6%).

Workup

  1. customat 25° C
  2. customNitrogen gas was bubbled through the reaction mixture for 15 minutes
  3. customthe tube was sealed
  4. temperatureThe reaction mixture was then cooled to 25° C.
  5. filtrationfiltered through celite
  6. washThe celite cake was washed with 10% methanol in DCM (30 ml)
  7. concentrationThe combined filtrate was concentrated under reduced pressure
  8. customto obtain a crude product, which
  9. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-ce42029069f64a40a846fc4e0f8341ba
Source dataset
uspto-grants-2015_02
Patent number
US08946432B2

Reaction notes

Loading…